I signed a voucher for a home on November 7th and it was turned in on November 8th.

Just trying to figure out what city or town will be good to invest in planning to live there for a year and then invest in another property and so on.

Not sure if you were looking for a long-term hold on a two family, but it seems that was not playing out favorably for you. 

However, profits would be bigger if there were no HOA fee and there would be more opportunity to make improvements on the property.

I think it depends on the problem.

If that isn't paid, it is a defacto lien on the property.

Also, you may charge a premium on the rent (higher rent) in this model of leasing.If you charge them a higher upfront option fee, it will demonstrate that the buyer is committed reduce the likelihood of default.

And the wall is built on top of that wood.

But how much do you spend annually on all these, just curious?

Quote from @John Kelly:I would agree with @Ashish Acharya, #1 is the best answer to the question on his response in the reason it would not be good to use an LLC on a house hack until you move out of the house and call it a true rental.